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Windsor

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Windsor Flights as Low as $180

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Cape Air
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 18 hours ago
$180
Roundtrip
found 18 hours ago
Select Cape Air flight, departing Mon, May 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, May 16, priced at $180 found 18 hours ago
Cape Air
Thu, May 28 - Mon, Jun 15
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$188 Roundtrip, found 2 days ago
$188
Roundtrip
found 2 days ago
Select Cape Air flight, departing Thu, May 28 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 15, priced at $188 found 2 days ago
Cape Air
Thu, May 14 - Mon, Jun 1
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$188 Roundtrip, found 18 hours ago
$188
Roundtrip
found 18 hours ago
Select Cape Air flight, departing Thu, May 14 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 1, priced at $188 found 18 hours ago
Cape Air
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$190 Roundtrip, found 18 hours ago
$190
Roundtrip
found 18 hours ago
Select Cape Air flight, departing Mon, May 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, May 16, priced at $190 found 18 hours ago
Cape Air
Thu, May 28 - Mon, Jun 15
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$194 Roundtrip, found 2 days ago
$194
Roundtrip
found 2 days ago
Select Cape Air flight, departing Thu, May 28 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 15, priced at $194 found 2 days ago
Cape Air
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$196 Roundtrip, found 18 hours ago
$196
Roundtrip
found 18 hours ago
Select Cape Air flight, departing Mon, May 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, May 16, priced at $196 found 18 hours ago
JetBlue Airways
Thu, May 28 - Mon, Jun 15
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$198 Roundtrip, found 2 days ago
$198
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, May 28 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 15, priced at $198 found 2 days ago
Cape Air
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$200 Roundtrip, found 18 hours ago
$200
Roundtrip
found 18 hours ago
Select Cape Air flight, departing Mon, May 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, May 16, priced at $200 found 18 hours ago
JetBlue Airways
Thu, May 28 - Mon, Jun 15
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$204 Roundtrip, found 2 days ago
$204
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, May 28 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 15, priced at $204 found 2 days ago
Cape Air
Thu, May 14 - Mon, Jun 1
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$205 Roundtrip, found 18 hours ago
$205
Roundtrip
found 18 hours ago
Select Cape Air flight, departing Thu, May 14 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 1, priced at $205 found 18 hours ago
JetBlue Airways
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$206 Roundtrip, found 18 hours ago
$206
Roundtrip
found 18 hours ago
Select JetBlue Airways flight, departing Mon, May 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, May 16, priced at $206 found 18 hours ago
Cape Air
Thu, May 14 - Mon, Jun 1
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$209 Roundtrip, found 18 hours ago
$209
Roundtrip
found 18 hours ago
Select Cape Air flight, departing Thu, May 14 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 1, priced at $209 found 18 hours ago
Cape Air
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$210 Roundtrip, found 18 hours ago
$210
Roundtrip
found 18 hours ago
Select Cape Air flight, departing Mon, May 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, May 16, priced at $210 found 18 hours ago
JetBlue Airways
Thu, May 14 - Mon, Jun 1
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$216 Roundtrip, found 18 hours ago
$216
Roundtrip
found 18 hours ago
Select JetBlue Airways flight, departing Thu, May 14 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 1, priced at $216 found 18 hours ago
JetBlue Airways
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$217 Roundtrip, found 18 hours ago
$217
Roundtrip
found 18 hours ago
Select JetBlue Airways flight, departing Mon, May 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, May 16, priced at $217 found 18 hours ago
Cape Air
Thu, May 14 - Mon, Jun 1
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$220 Roundtrip, found 18 hours ago
$220
Roundtrip
found 18 hours ago
Select Cape Air flight, departing Thu, May 14 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 1, priced at $220 found 18 hours ago

Cheap Flights to Windsor

Fall in love at first flight with your vacation to Windsor by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Windsor on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Windsor, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Windsor

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Windsor with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the VSF airport.

What is the cheapest month to fly to Windsor?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Windsor are in May, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Windsor?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Windsor.

What airport is best to fly into Windsor?

When you’re planning your trip to Windsor, convenience is the name of the game. Luckily, Windsor Lebanon Municipal Airport is nearby so you can deplane and get going on checking off everything on your Windsor must-do list.

How much are flights to Windsor?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Windsor on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $180, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Windsor?

The trick to saving a stack of cash on your flight to Windsor? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $180 right now, why wait?

Windsor Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$180

Last Minute Hotel Deals in Windsor

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
Book a stay at this golf hotel in Killington. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the ...
7.4/10 Good! (1,002 reviews)
Yes

Reviewed on Mar 19, 2026

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Killington Mountain Lodge, Tapestry Collection by Hilton
White River Inn and Suites

White River Inn and Suites

2.5 out of 5
91 Ballardvale Drive White River Junction VT
Book a stay at this business-friendly hotel in White River Junction. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
7/10 Good! (1,002 reviews)
The room had a food smell. There were little black flies in the room. When I notified the desk the gentleman said he would be sure to report it to the proper person. No offer of a discount on the price of the room or even a voucher for a future stay which I never would have used. Not interested in ...

Reviewed on Mar 15, 2026

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White River Inn and Suites
Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

2.5 out of 5
25 Airport Road West Lebanon NH
Book a stay at this business-friendly hotel in West Lebanon. Enjoy free WiFi, free parking, and room service. Our guests praise the breakfast and the pool in ...
8.2/10 Very Good! (1,002 reviews)
Very convenient location. Helpful, kind staff.

Reviewed on Mar 17, 2026

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Fireside Inn & Suites West Lebanon
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
Book a stay at this business-friendly hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9.4/10 Exceptional! (1,138 reviews)
Absolute perfect stay, Chelsea was so kind and helpful. The room was immaculate and cozy. This is always our go to when in the area.

Reviewed on Mar 17, 2026

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Align Inn Vermont
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
Book a stay at this spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (1,002 reviews)
Clean, comfortable and quiet. Great retreat for skiers. Nice hot tub, comfy beds and convenient parking.

Reviewed on Mar 19, 2026

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Pointe at Castle Hill Resort
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (569 reviews)
Excellent!!

Reviewed on Mar 18, 2026

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Woodstock Inn & Resort
Holiday Inn Express Hotel & Suites White River Junction by IHG

Holiday Inn Express Hotel & Suites White River Junction by IHG

2.5 out of 5
121 Ballardvale Dr White River Junction VT
Book a stay at this business-friendly hotel in White River Junction. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the ...
8.6/10 Excellent! (1,001 reviews)
The bed was very uncomfortable and the room was hot

Reviewed on Mar 14, 2026

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Holiday Inn Express Hotel & Suites White River Junction by IHG
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr Killington VT
Book a stay at this family-friendly hotel in Killington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff ...
8.6/10 Excellent! (1,001 reviews)
Really friendly and helpful staff. Excellent bar and grille, pool and exercise room with generous hours. A little noisy as some parents let their kids free range about. However, very comfortable room, beds and great views.

Reviewed on Mar 19, 2026

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North Star Lodge and Resort
See all 2,704 properties in Windsor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.